In 1995, the U.S. Fish and Wildlife Service implemented an adaptive harvest management program (AHM) for the sport harvest of midcontinent mallards (Anas platyrhynchos). The program has been successful in reducing long-standing contentiousness in the regulatory process, while integrating science and policy in a coherent, rigorous, and transparent fashion. After 20 years, much has been learned about the relationship among waterfowl populations, their environment, and hunting regulations, with each increment of learning contributing to better management decisions. At the same time, however, much has been changing in the social, institutional, and environmental arenas that provide context for the AHM process. Declines in hunter numbers, competition from more pressing conservation issues, and global-change processes are increasingly challenging waterfowl managers to faithfully reflect the needs and desires of stakeholders, to account for an increasing number of institutional constraints, and to (probabilistically) predict the consequences of regulatory policy in a changing environment. We review the lessons learned from the AHM process so far, and describe emerging challenges and ways in which they may be addressed. We conclude that the practice of AHM has greatly increased an awareness of the roles of social values, trade-offs, and attitudes toward risk in regulatory decision-making. Nevertheless, going forward the waterfowl management community will need to focus not only on the relationships among habitat, harvest, and waterfowl populations, but on the ways in which society values waterfowl and how those values can change over time.